A Summer of New Experiences Ch. 02

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Jeannie shares an evening of exploration with Timmy.
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Part 2 of the 4 part series

Updated 06/08/2023
Created 12/23/2017
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Jeff and I didn't get to mess around again for several days. We accompanied Pops to his office during the day. Pops enjoyed having us in the office with him and we enjoyed going. There were always a few old war stories with a few good life lessons thrown in along the way. We also enjoyed his visiting with his office staff, Lucy and Debbie. If one didn't know my grandfather better, one would assume he was a cad. He never seemed to hire an assistant unless she was drop dead gorgeous, and preferably blonde. He said that they were remarkably efficient, but I often thought that was by sheer luck, not design. I had never seen him do anything inappropriate though, and I knew that every one of the girls that worked for him over the years, he'd had helped significantly. He was just a kind, old man with a big heart and an eye for a smart, pretty girl that needed a hand.

I'm sure he'd changed little over the years. He'd met our Granny, Tish, at a base dance during the war. She was a pretty, vivacious English girl and was working at a munitions factory, adjacent to his air base. Somehow, she eventually fell in love with this crazy B-17 pilot from Texas. He told her that he would he would always come home to her, through all the fires of hell and everything the Luftwaffe could throw at him. She had believed, but she always worried.

Granny's parents and two little sisters had been killed in her home town of Coventry in November 1940. She had been at work on the night shift in another munitions factory, when the raid occurred. Ironically, the German pilots had missed the factory she was working in and leveled her adjacent home neighborhood. She had told us over the years about the guilt she'd felt afterwards. She'd said that she finally had come to peace with it one spring day in 1945. That was the day she saw Pops' B-17 wing in low over the base for the last time after a big raid on Berlin. Pops asked her for her hand that day and they were married soon after they made it back home to the ranch outside Midland.

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The evenings that first week, we were hanging out with Jeannie. If it was possible, she more pretty and sexy than she had been the last time I'd seen her. I was curious if she was still as shy as she was last summer. We never seemed to find ourselves alone so that I could find out. Likewise, Jeff and I never found ourselves alone either. As it turned out, summer vacation was about to get even more interesting.

That Friday night, we had reservations at a steakhouse owned by friends of my grandparents. It was a nice place, so we all dressed accordingly. Jeff and I were wearing slacks and button up shirts. I wore some leather loafers with no socks. My grandparents, Jeff and I loaded up in Pop's conversion van and drove down the street to pick up Aunt Barbs and Jeannie. Jeannie was wearing a very pretty red dress, tan nylons and sexy, black heels. She looked amazing. We smiled at each other when she got in.

"What," she asked with a smile.

"Nothing, you look really great tonight." I said, smiling back.

"Thanks." She grinned at me.

We arrived at the restaurant and were seated in a big booth. Jeff and Jeannie were seated on either side of me. Just as we got our salads, I felt a smooth and silky foot sliding around my ankle. I looked over at her, but Jeannie was just looking at our grandmother as she told a story about one of the charities she helped with. Her face was vacant as she nibbled on some lettuce. As we continued to listen, I felt her foot push its way up my pants and start rubbing higher on my calf.

I had long been a fan of legs in nylon and had even tried my mom's pantyhose on many times. I loved the way they felt. Jeannie had great legs and I always loved seeing her wear them. She continued stroking my leg even through dessert. After Pops paid the bill, we filed out and back out to the van.

Jeannie got to the van ahead of Jeff and me. She got in first and crawled in the back seat, where Jeff and I had sat on the way to dinner. I joined her and we were soon headed back home. It was dark by then, and it would be a 45-minute drive back home. I noticed within 5 minutes, both Jeff and Aunt Barbs were asleep in the seat in front of us. Jeannie scooted over a little bit and leaned her head on my shoulder. She had done that so many times on car rides. I whispered to her, "are you sleepy, too?"

"No, not really." She answered. My left arm was still between us. It was uncomfortable so I moved it, thinking I would put it across the back of the seat. When I moved, she reached up and pulled my arm around her shoulders. She surprised me by then stretching her legs across mine and snuggling in closer.

"Would you mind rubbing my feet?" She whispered. "These shoes are a little too small now and they pinch my feet. That's why I took them off at dinner."

"Sure," I whispered back. That explained why she took her shoes off, but not why she was teasing me with her nylon covered foot, I thought! I took her shoes off and sat them on the floor of the van. I started with her cute little right foot. I could tell with the traffic lights, her toe nails were painted a bright red. I thought that was sexy as hell peaking trough her nylons. I began to rub her foot and I could feel the indentions where her shoes had pinched her feet. I massaged those areas slowly and I saw her smile.

I couldn't believe I was sensuously rubbing her sexy feet, not three feet from her sleeping mother and brother. I guess I should have been able to, after all her brother and I had done a few days before.

"That feels really great, thanks," she whispered.

I just smiled at her in the darkness, since I was having the time of my life. I'd never had the opportunity to experience touching a silky pair of legs, and I made up for it that night. I took my left arm from around her so that I could have both hands. My massage soon moved away from her pretty little feet to her firm calves. Her gymnastics career had developed quite a set of legs. My hands glided up and down both silky calves, but I always stopped at her knees. I could sense some impatience on her part each time I stopped.

"I might need massaged a little further up too." She whispered her suggestion in my ear.

I looked at her, my face a question. She simply nodded yes. She took my left hand and brought my arm back around her shoulders. I squeezed her closely to me as my right hand again approached her knee. This time my hand glided up past her knee and just under the hem of her skirt. I traced my way back down on the other supple thigh. I continued like that for a while. Even though she had said it was okay, I didn't want to go too far, given her shyness the previous summer.

She shifted around a bit in the seat and her knees parted ever so slightly. She looked up at me and when our eyes met, she nodded again. From her knee, my hand glided up the inside of her nylon covered thigh. I got about as far as before and prepared to stop. She responded by opening her legs more. Now I faced a decision. Should I? I looked at her again. She was watching me intently. I felt her shift around some more and felt her legs part even further. That made up my mind for me. My hand continued up between her pantyhose clad thighs. I soon reached where they met.

I began to gently rub the very tops of her thighs. Along that little crease where they met her hips. The pantyhose held her so tightly and I loved the way she felt through them. My hand grazed her pantyhose-covered pussy and I heard her let her breath out slowly. As I rubbed around with my fingers, I realized the pantyhose she was wearing were very sheer. They weren't the control-top type that my mom wore and that I was familiar with from my own experimentation. There was just a single seam where the two legs joined and it didn't seem that they had the little cotton piece that was usually found in gusset. I found myself wondering what she looked like in them under her dress. I continued to rub and explore, before I finally realized that she was not even wearing panties. I lightly rubbed the lips of her womanhood and looked at her. She simply smiled.

I felt her wetness with the tips of my fingers. It was driving me wild to be touching her like that. I felt the van slow and I realized Pops was exiting I-20. We'd be home in about 15 minutes.

Knowing time was not on my side, I wanted to make the most of this experience. I circled her clit with my thumb as I cupped her mound in my hand, lightly rubbing her labia. It was difficult since I had my hand up her dress at an awkward angle. She was getting fidgety and was squirming around against me. I realized my cock was painfully hard in my slacks, but all but forgotten as I touched my sexy cousin in her most intimate spot. Her movement caused her silky, leg to brush against my cock. She noticed what had happened. I had hoped she would grab it, but she didn't. She just rubbed it with her leg. As I usually preferred, I hadn't worn underwear and her silky leg was sliding up and down my cock with only the fabric of my slacks separating the two.

I continued to rub her and I watched as she closed her eyes. I really wanted to get her off like I did Katie the previous summer. The van turned off the state highway towards my grandparent's house. We were going to be home any minute. I knew she was going shopping the next morning with Barbs and Sandy, so I figured she'd stay at her own house. I redoubled my efforts hoping I wasn't too rough with her. I felt Jeannie quiver and she grabbed my right forearm. She pushed her face against my chest. I felt a sharp pain and almost yelled in surprise. She had bit me! She looked back up just as Pops turned into the neighborhood.

"I'm sorry about that," she whispered. I smiled and shook my head.

She sat up and got her shoes back on. We stopped first to let Aunt Barbs out. She and Jeff had finally woken up. Jeff murmured something about going with me to our grandparents, but his mom insisted he stay home that night. I figured Jeannie would get out too. The rest of my night was going to be Uncle Billy's magazine collection and my own right hand, I thought.

"Mom, I'm going to spend the night at Pops and Granny's tonight." Jeannie said, much to my surprise.

"Ok, but you and Timmy need to go to bed, and not stay up late. We're going to leave early for our shopping trip." Barbs reminded her.

"I know Mom. We won't stay up too late." Jeannie said.

"Goodnight, Barbs," I added.

"Night, Timmy," She replied.

We got to my grandparents and all walked in the house. My grandparents announced they were going to turn in. Their bedroom was on the other side of the huge house, so providing we didn't set off a bomb, we weren't likely to disturb them. I followed Jeannie up the stairs, admiring her shapely legs in those silky pantyhose.

"You want to go swimming?" She asked, when we reached the upstairs landing.

"Yeah, but it's getting late. Your mom told us..." I tried to reply.

"Would you stop??" She cut me off. "I'm not tired, are you?"

"No, not really." I replied.

"Then let's do it!!" She smiled.

She turned to go to Aunt Leslie's bedroom. I grabbed my trunks from my bathroom and walked into the middle bedroom that was "mine". As I undressed, my cock was still really hard. I'd loved touching Jeannie in the van. I couldn't wait to see what the rest of the night would bring. When I was naked, I looked in the dresser mirror and saw the bite mark she'd left on my chest. It was very prominent. I'd have to ask her what that was all about!

I was dressed and waiting for her, when she walked out Leslie's bedroom. She was wearing one of Leslie's sexy coverups and she had her up in a bun.

"Let's go!" She took my hand and led me down the stairs. We went outside and I went to turn on the pool lights, but she stopped me. "No, we don't need those tonight."

"Okay," I smiled.

She walked over to the refrigerator in the outdoor kitchen and when she turned around, I realized she had grabbed a few beers.

"Beer, huh?" I smiled.

"Yeah, sure. You know Pops doesn't mind, as long as we're not driving." She smiled and handed them to me to carry.

"Cool." I said.

She dropped her coverup on a lounge chair. She was facing me, and I noticed that she was not wearing the same black bikini she had the other day. This one was bright orange.

"Did you get another one?" I asked curiously.

"Oh, no. This one is Leslie's. Mom would never let me wear one like this!" She turned around and I immediately saw why. The back of the bottom was just a thin bit of fabric that ran up between her sexy ass cheeks.

"Oh, wow." I managed to gasp. There was that amazing ass, heart-shaped, perfect, and completely bare.

"You like it?" She asked.

"Fuck yeah, I mean, Yeah. You look great, Jeannie. It's just so damn sexy."

"I'll accept that, I think." She smirked. "It's a little big. I'm not as big as her on top." She tugged on the bikini top for emphasis.

"Maybe, but you still look hot as hell!" I smiled.

"Thank you. You're always know what to say to me. You're not like those dorks I went to school with." She grinned.

"They haven't seen you like this." I added.

She smiled, took my hand again and we walked to the pool. I stuck my foot in it.

"It's cold!" I warned.

"Maybe we should just get in the hot tub, then." She suggested.

"Fine with me." The hot tub was built in a redwood gazebo. It had walls that could be folded up in winter, so you could use it year around. Since it was still early in the summer, only one side was down. We stepped in the hot tub and sat down.

"This is much better," Jeannie said. I agreed. We both opened a beer and enjoyed a few sips of the venerable Budweiser.

"So, what exactly were you guys doing in pool the other day?" She asked. I thought maybe we'd talk about the van ride home, not Tuesday afternoon.

"It was nothing, Jeannie!" I said, defensively.

"It didn't look like nothing, Tim. I know what I thought it looked like." She laughed.

"Which was?"

"What I said! That you guys were screwing!" She laughed.

"We weren't really screwing, Jeannie!" I countered.

"Uh huh. I didn't know you two liked boys." She smiled.

"We don't really like boys, but we were both just excited and then things happened."

"I see." She smiled suspiciously. "Why were you guys all excited?"

"Well, for me it was a couple things. You looked so damn sexy in that bikini and I was also naked in the pool, and I got excited. I don't know about Jeff."

"Never mind him. There's no telling with that jackass. I'm glad I had an effect on you, though." She said.

"You are, huh?" I smiled.

"Yeah. I love that I turn you on." She had a mischievous smile on her face.

"I'm your cousin, though." I laughed.

"Duh! I know that, but you're always sweet and nice to me. You're not like the guys at school. You're polite and a gentleman. All they want to do is feel me up and try to bang me."

"I was feeling you up tonight." I countered.

"Yes, but I wanted you to. I asked you to and you were nice about it. I had to tell you that it was okay to go further. That's different than them. Did you like doing it?" She asked.

"Of course, I loved it." I replied.

"Have you felt up a lot of girls?" She asked. I briefly explained my history, excluding Katie.

"How about you? You messed around much?" I asked.

"A bit. Mostly just kissing and stuff. If I hadn't stopped a lot of guys, I would have been a lot further." She rolled her eyes. "Like I said most guys I've been out with are just awful. Tonight, was a real first for me."

"Oh?" I asked.

"Yeah, it was. You got me off, really good." She smiled.

"I'm glad to hear that. But why did you bite me?" I asked.

"To keep from screaming! You don't know how amazing that felt!" She said.

"It kinda hurt," I joked.

"Oh, poor baby. I'm so sorry." She said. She started rubbing my chest where she'd bit me. I loved feeling her soft hands on me. I hoped she'd never stop. "I'm really glad you're here though."

"Why?"

"I just told you. You're nice and sweet. We can have fun and I don't have to worry about you telling the whole school about everything. Sandy gave a guy blow job last year and people are still teasing her about it." She replied.

"Oh, that sucks for her." I said.

"Tell me about it. Do you want to do more with me?" She asked.

"Well yeah, of course I do. Do you? I don't want you to feel weird about it."

She groaned. "Gawd, yes, of course I want to. Are you even listening to me? You love and care about me. You've always treated me like a princess. And you won't go bragging about it to everyone. Besides you were already trying to screw my brother the other day! You don't think that's weird?"

"Haha. Yeah, I guess I see what you mean." I admitted.

"Plus, I know what you and Katie were doing that night last summer."

"What? Did you see us?" I asked, surprised.

"No, silly. Girls talk to one another too." She explained. I should have figured.

"Oh. I see. I mean it just kind of happened." I added. "I figured after the day at the ranch nothing else would happen last summer since I was going home."

"It's fine. I was pretty shy last summer. I didn't feel the way I do now." She said.

"What changed?" I asked.

She reached up and cupped her boobies.

"Well, I started to fill out more, and I started feeling more confident. Katie has been coaching me on that."

"That's good, you should feel good about yourself. You're really hot, Jeannie." I said.

"Thank you. You've always been so sweet to us. You don't how much that helps." She reached over and hugged me. I enjoyed the thrill of her bikini-covered breasts against my chest. I was so hard for her.

"So, seriously, what else happened the other day after I left?" She asked. She was just so back and forth, I felt like I was being interrogated.

Jeff and I hadn't really sworn any oaths to one another, but I had heard the phrase "don't kiss and tell".

"I don't think I should say." I said, taking another drink of beer to hide my uneasiness. I'd really enjoyed what Jeff and I had shared, but I didn't want to freak her out.

"Really? What did you perverts do?" She smiled eagerly, her face alight with wonder.

"Hey, we're not perverts. We just messed around a bit. Nothing too much." I said.

"You're lucky it's dark out here, because I bet you're blushing!! You two were in the pool house with the door locked a long time!!" She laughed and took a swig of her beer.

"How do you know that? I thought you went to the mall!" I exclaimed.

"No, we didn't. Sandy's Mom had a migraine. We hung out for a while and then I came back. I figured you guys would still be in the pool, so I thought I'd join you. When I saw Pops and Granny were gone and you two weren't in the pool, I went upstairs and saw you all had been in Billy's room. I figured something had happened in there. Especially when I saw all of those filthy magazines lying on the bed!"

I was glad it was dark too, because I had to be red as a beet.

She continued, "Tim, it's ok. I know Jeff and his friends jerk off together. Sandy caught them this spring. It's no big deal. I just like teasing you about it." She had dangled the bait, then she started to set the hook. "So, what happened after you jerked off together?"

"We didn't jerk off together." I said, which was completely true. "How do you know something happened?"

"You two were in the pool house with the shower running for at least 30 minutes!!" She said seriously.

"So?" I asked.

"Neither of you has ever taken a 30-minute shower, not to mention together." She said.

"Okay, geez. I'll tell you." She scooted over next to me. She leaned in with anticipation, her sexy boobs were just inches from me. "But you have to promise, you'll never tell anyone."

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